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【结 构 式】 
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【分子编号】35219 【品名】4-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)carbonyl]benzoic acid 【CA登记号】 |
【 分 子 式 】C23H26O3 【 分 子 量 】350.45764 【元素组成】C 78.83% H 7.48% O 13.7% |
与该中间体有关的原料药合成路线共 2 条
合成路线1
该中间体在本合成路线中的序号：(I)
| 【1】 Faul, M.M.; Ratz, A.M.; Sullivan, K.A.; Trankle, W.G.; Winneroski, L.L.; Synthesis of novel retinoid X receptor-selective retinoids. J Org Chem 2001, 66, 17, 5772. |
| 【1】 WeiL．Yang H，ZhuQIn. 2003．Preparation of bexarotene antitunnr agent发明专利申请公开说明书，CN 1429807 |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 35219 | 4-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)carbonyl]benzoic acid | C23H26O3 | 详情 | 详情 | |
| (I) | 35217 | 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene | C15H22 | 详情 | 详情 | |
| (II) | 66155 | Benzoic acid,4-[1-hydroxy-1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethyl]- | 852524-20-0 | C24H30O3 | 详情 | 详情 |
| (II) | 60252 | 6-bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene | C15H21Br | 详情 | 详情 | |
| (III) | 60253 | 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenylboronic acid | C15H23BO2 | 详情 | 详情 | |
| (IV) | 60255 | methyl 4-acetylbenzoate | C10H10O3 | 详情 | 详情 | |
| (V) | 60254 | methyl 4-(1-{[(trifluoromethyl)sulfonyl]oxy}ethenyl)benzoate | C11H9F3O5S | 详情 | 详情 | |
| (VI) | 60246 | methyl 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)ethenyl]benzoate | C25H30O2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VI)Friedel-Crafts condensation of 2,5-dichloro-2,5-dimethylhexane (I) with toluene (II) in the presence of AlCl3 or FeCl3 afforded the tetrahydronaphthalene (III). Subsequent acylation of (III) with monomethyl terephthalic acid chloride (IV) provided keto ester (V), which was hydrolyzed to keto acid (VI) with methanolic KOH. Condensation of (VI) with hydroxylamine hydrochloride gave the corresponding oxime as a mixture of geometric isomers. The required Z isomer was then isolated by recrystallization from chloroform/hexane.
| 【1】 Faul, M.M.; Ratz, A.M.; Sullivan, K.A.; Trankle, W.G.; Winneroski, L.L.; Synthesis of novel retinoid X receptor-selective retinoids. J Org Chem 2001, 66, 17, 5772. |
| 【2】 Boehm, M.F.; Canan Koch, S.S.; Cesario, R.M.; Dardashti, L.J.; Nadzan, A.M.; Croston, G.E.; Heyman, R.A.; Synthesis of retinoid X receptor-specific ligands that are potent inducers of adipogenesis in 3T3-L1 cells. J Med Chem 1999, 42, 4, 742. |
| 【3】 Zhang, L.; Boehm, M.F.; Badea, B.A.; White, S.K.; Mais, D.E.; Berger, E.; Suto, C.M.; Goldman, M.E..; Heyman, R.A.; Synthesis and structure-activity relationships of novel retinoid X receptor-selective retinoids. J Med Chem 1994, 37, 18, 2930. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 32201 | Hydroxylamine | 7803-49-8 | H3NO | 详情 | 详情 | |
| (I) | 35216 | 2,5-dichloro-2,5-dimethylhexane | C8H16Cl2 | 详情 | 详情 | |
| (II) | 12890 | Toluene | 108-88-3 | C7H8 | 详情 | 详情 |
| (III) | 35217 | 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene | C15H22 | 详情 | 详情 | |
| (IV) | 25029 | p-Phthalic acid monomethyl ester chloride; Terephthalic acid monomethyl ester chloride; Methyl 4-chlorocarbonylbenzoate | 7377-26-6 | C9H7ClO3 | 详情 | 详情 |
| (V) | 35218 | methyl 4-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)carbonyl]benzoate | C24H28O3 | 详情 | 详情 | |
| (VI) | 35219 | 4-[(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)carbonyl]benzoic acid | C23H26O3 | 详情 | 详情 |
Extended Information